Rational Synthesis of Some New para-Aminobenzoic Acid Hybrids with Thiazolidin-2,4-diones with Antimicrobial Properties. ADMET and molecular docking evaluation

Abstract

The present paper presents the synthesis, physicochemical characterization, in vitro antimicrobial activity and the molecular docking study of a series of ten new thiazolidine-2,4-dione derivatives conjugated to para-aminobenzoic acid (PABA). The lipophilicity of the new molecules was evaluated in silico. Quantitative elemental C, H, N, S analysis and spectral data (mass spectrometry, infrared and nuclear magnetic resonance) were consistent with the expected data. The results of the antimicrobial activity screening revealed that some of the synthesized compounds had moderate to good activity against E. coli ATCC 25922, S. aureus, ATCC 6538P and C. albicans ATCC 10231.

Design, Synthesis and Biological Evaluation of New Piperazin-4-yl-(acetyl-thiazolidine-2,4-dione) Norfloxacin Analogues as Antimicrobial Agents

“…The procedure applied for the synthesis of the intermediate compounds 5a – e was performed using a previously reported protocol [47] and the structural data were consistent with the previously reported characterizations [47,48,49].…”

SYNTHESIS AND IN SILICO APPROACHES OF NEW SYMMETRIC BIS-THIAZOLIDINE-2,4-DIONES AS Ras AND Raf ONCOPROTEINS INHIBITORS

“…The route of synthesis followed to obtain the final compounds 5a-j is presented in Figure 1. Firstly, the intermediate compounds 3a-j were obtained after a Knoevenagel condensation between some (hetero)aromatic aldehydes (1a-j) and thiazolidine-2,4-dione (2) using a previously reported protocol [30,46,55]. To obtain the final compounds 5a-j, 2 mmol of intermediate compounds 3a-j were mixed with 1 mmol (0.127 g) of 1,3-dichloroacetone (4), 1 mmol (0.166 g) of anhydrous KI and 2 mmol (0.276 g) of K2CO3 in 5 mL of DMF in a glass flask as previously reported by our group [32].…”

“…The three-dimensional structures of the targeted proteins were taken from RCSB Protein Data Bank (PDB) [3]. The molecular docking studies were performed against the A chain fragment of the deposited macromolecules, with the proper preliminary preparation of the macromolecules, according to the previously reported protocol [30,35]. 20 poses were generated for each ligand in all three macromolecules binding sites.…”

“…The study of TZD hybrids from the point of view of their in silico design, chemical synthesis, investigation of their antitumor, antidiabetic, antiinflammatory, antioxidant and antimicrobial activities, has enabled the discovery of very promising and druglike candidates. Considering the aspects presented above and our previous experience in the synthesis of hybrid thiazolidine-2,4-dione derivatives and in the investigation of their antimicrobial [30,36], anti-inflammatory [38], antioxidant [18,31] and antitumour [37] potential, our aim in this work was to obtain new symmetric bis-thiazolidine-2,4-diones and to evaluate, in silico, their capacity to inhibit Raf and Ras oncoproteins, as potential antitumor drug candidates.…”

4-Aminobenzoic Acid Derivatives: Converting Folate Precursor to Antimicrobial and Cytotoxic Agents

“…PABA hybrid compounds have been reported as potential antimicrobial agents. PABA has been linked with other bioactive scaffolds involving NH 2 group via amide bond [15], as a secondary amine [1] or ureido moiety [16]. The derivatives of PABA showed improved radical scavenging properties and also enhanced toxicity for cancer cells [5].…”